CN1028169C - 直接分离巯甲丙脯酸的方法 - Google Patents

直接分离巯甲丙脯酸的方法 Download PDF

Info

Publication number: CN1028169C
Authority: CN; China
Prior art keywords: aqueous solution; captopril; hydroxide; carry out; reactant
Prior art date: 1989-11-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CN90108901A

Other languages

English (en)

Chinese (zh)

Other versions

CN1051908A (zh

Inventor

尼尔·G·安德森

戴维·A·勒斯特

巴巴拉·J·贝内特

阿伦·F·费尔德曼

罗伯特·E·波隆斯基

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

ER Squibb and Sons LLC

Original Assignee

ER Squibb and Sons LLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-11-06

Filing date

1990-11-06

Publication date

1995-04-12

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=23714462&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN1028169(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1990-11-06 Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC

1991-06-05 Publication of CN1051908A publication Critical patent/CN1051908A/zh

1995-04-12 Application granted granted Critical

1995-04-12 Publication of CN1028169C publication Critical patent/CN1028169C/zh

2005-11-06 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 56
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 title abstract description 40
229960000830 captopril Drugs 0.000 title abstract description 39
239000000376 reactant Substances 0.000 claims abstract description 17
239000007864 aqueous solution Substances 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 14
230000008569 process Effects 0.000 claims abstract description 12
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
239000001257 hydrogen Substances 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
239000003456 ion exchange resin Substances 0.000 claims abstract description 6
229920003303 ion-exchange polymer Polymers 0.000 claims abstract description 6
150000003839 salts Chemical class 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 5
239000011707 mineral Substances 0.000 claims abstract description 5
238000006386 neutralization reaction Methods 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 26
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
150000001875 compounds Chemical class 0.000 claims description 8
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 3
239000003729 cation exchange resin Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 2
229910001415 sodium ion Inorganic materials 0.000 claims description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 3
NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims 3
229910001414 potassium ion Inorganic materials 0.000 claims 3
229910052744 lithium Inorganic materials 0.000 claims 2
229910001416 lithium ion Inorganic materials 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
230000007935 neutral effect Effects 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 12
239000012535 impurity Substances 0.000 abstract description 12
239000003960 organic solvent Substances 0.000 abstract description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 5
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 3
238000002955 isolation Methods 0.000 abstract description 3
238000011282 treatment Methods 0.000 abstract description 2
239000011701 zinc Substances 0.000 abstract description 2
229910052725 zinc Inorganic materials 0.000 abstract description 2
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 abstract 1
239000000243 solution Substances 0.000 description 20
238000002425 crystallisation Methods 0.000 description 15
230000008025 crystallization Effects 0.000 description 15
239000000047 product Substances 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
-1 alkali metal salt compound Chemical class 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
239000012266 salt solution Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910001413 alkali metal ion Inorganic materials 0.000 description 2
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 2
229910052728 basic metal Inorganic materials 0.000 description 2
150000003818 basic metals Chemical class 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000003292 glue Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000009413 insulation Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000002002 slurry Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000005541 ACE inhibitor Substances 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Chemical group 0.000 description 1
244000309464 bull Species 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
HIZCIEIDIFGZSS-UHFFFAOYSA-N carbonotrithioic acid Chemical compound SC(S)=S HIZCIEIDIFGZSS-UHFFFAOYSA-N 0.000 description 1
239000002327 cardiovascular agent Substances 0.000 description 1
229940125692 cardiovascular agent Drugs 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000011549 crystallization solution Substances 0.000 description 1
238000011026 diafiltration Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002500 ions Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
238000009401 outcrossing Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Chemical group 0.000 description 1
238000009700 powder processing Methods 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229960002429 proline Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
238000006479 redox reaction Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000010025 steaming Methods 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Compounds Of Unknown Constitution (AREA)
Pyrrole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Semiconductor Lasers (AREA)

CN90108901A 1989-11-06 1990-11-06 直接分离巯甲丙脯酸的方法 Expired - Fee Related CN1028169C (zh)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/432,028 US5026873A (en)	1989-11-06	1989-11-06	Process for direct isolation of captopril
US432,028		1989-11-06

Publications (2)

Publication Number	Publication Date
CN1051908A CN1051908A (zh)	1991-06-05
CN1028169C true CN1028169C (zh)	1995-04-12

Family

ID=23714462

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CN90108901A Expired - Fee Related CN1028169C (zh)	1989-11-06	1990-11-06	直接分离巯甲丙脯酸的方法

Country Status (29)

Country	Link
US (1)	US5026873A (pt)
EP (1)	EP0427435B1 (pt)
JP (1)	JPH03169856A (pt)
KR (1)	KR0163956B1 (pt)
CN (1)	CN1028169C (pt)
AT (1)	ATE119148T1 (pt)
AU (1)	AU635341B2 (pt)
CA (1)	CA2027377A1 (pt)
CY (1)	CY1852A (pt)
CZ (1)	CZ277714B6 (pt)
DE (1)	DE69017355T2 (pt)
DK (1)	DK0427435T3 (pt)
EG (1)	EG18964A (pt)
ES (1)	ES2068349T3 (pt)
FI (1)	FI98814C (pt)
HK (1)	HK109895A (pt)
HU (1)	HU208525B (pt)
IE (1)	IE67284B1 (pt)
IL (1)	IL96018A (pt)
MX (1)	MX166721B (pt)
MY (1)	MY106445A (pt)
NO (1)	NO904796L (pt)
NZ (1)	NZ235958A (pt)
PH (1)	PH26962A (pt)
PL (1)	PL287642A1 (pt)
PT (1)	PT95781B (pt)
RU (1)	RU2001909C1 (pt)
SK (1)	SK278604B6 (pt)
ZA (1)	ZA908523B (pt)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN107652215A (zh) *	2017-09-19	2018-02-02	重庆西南制药二厂有限责任公司	一种卡托普利的制备方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU208954B (en) *	1990-09-21	1994-02-28	Egyt Gyogyszervegyeszeti Gyar	Process for producing 1-(3-mercapto-(2s)-methyl-1-oxo-propyl)-l-prolyn
US5387697A (en) *	1994-06-13	1995-02-07	Merck & Co., Inc.	Process for the preparation of 1-[3-acetylthio-2(s)-methylpropanoyl]-l-proline
JP3980684B2 (ja) *	1996-10-11	2007-09-26	株式会社カネカ	高品質カプトプリルの簡便な製造方法
CN110146624B (zh) *	2019-06-14	2022-02-22	湖南汉森制药股份有限公司	一种卡托普利有关物质的检测方法
CN110950792A (zh) *	2019-12-11	2020-04-03	华中药业股份有限公司	一种卡托普利的改进制备方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4105776A (en) *	1976-06-21	1978-08-08	E. R. Squibb & Sons, Inc.	Proline derivatives and related compounds
AU509899B2 (en) *	1976-02-13	1980-05-29	E.R. Squibb & Sons, Inc.	Proline derivatives and related compounds
US4241076A (en) *	1978-02-21	1980-12-23	E. R. Squibb & Sons, Inc.	Halogenated substituted mercaptoacylamino acids
NL7809120A (nl) *	1978-09-07	1980-03-11	Oce Andeno B V Grubbenvorsterw	Werkwijze voor de bereiding van proline-derivaten.
US4297282A (en) *	1979-03-02	1981-10-27	Sumitomo Chemical Company, Limited	Resolution of mercaptopropionic acids
HU184082B (en) *	1979-12-29	1984-06-28	Egyt Gyogyszervegyeszeti Gyar	Process for preparing 1-3-/3mercapto-/2s/-methyl-propinyl/-pyrrolidine-/2s/-carboxylic acid
US4332726A (en) *	1980-08-25	1982-06-01	E. R. Squibb & Sons, Inc.	Purification of mercaptoacyl amino acids
JPS58124764A (ja) *	1982-01-20	1983-07-25	Kanegafuchi Chem Ind Co Ltd	光学活性チオ−ル化合物の製造法
KR870001570B1 (ko) *	1984-12-19	1987-09-04	보령제약 주식회사	피롤리딘 유도체의 제조방법
IL91581A (en) *	1988-09-13	1993-07-08	Sepracor Inc	Methods for preparing optically active captopril and its analogues

1989
- 1989-11-06 US US07/432,028 patent/US5026873A/en not_active Expired - Lifetime
1990
- 1990-10-10 AU AU63977/90A patent/AU635341B2/en not_active Ceased
- 1990-10-11 CA CA002027377A patent/CA2027377A1/en not_active Abandoned
- 1990-10-11 MY MYPI90001775A patent/MY106445A/en unknown
- 1990-10-16 PH PH41385A patent/PH26962A/en unknown
- 1990-10-16 IL IL9601890A patent/IL96018A/en not_active IP Right Cessation
- 1990-10-19 IE IE375990A patent/IE67284B1/en not_active IP Right Cessation
- 1990-10-24 ZA ZA908523A patent/ZA908523B/xx unknown
- 1990-10-29 DK DK90311824.8T patent/DK0427435T3/da active
- 1990-10-29 ES ES90311824T patent/ES2068349T3/es not_active Expired - Lifetime
- 1990-10-29 AT AT90311824T patent/ATE119148T1/de not_active IP Right Cessation
- 1990-10-29 DE DE69017355T patent/DE69017355T2/de not_active Expired - Fee Related
- 1990-10-29 EP EP90311824A patent/EP0427435B1/en not_active Expired - Lifetime
- 1990-10-31 MX MX023131A patent/MX166721B/es unknown
- 1990-11-02 CZ CS905405A patent/CZ277714B6/cs not_active IP Right Cessation
- 1990-11-02 SK SK5405-90A patent/SK278604B6/sk not_active IP Right Cessation
- 1990-11-04 EG EG600690A patent/EG18964A/xx active
- 1990-11-05 NZ NZ235958A patent/NZ235958A/xx unknown
- 1990-11-05 RU SU904831477A patent/RU2001909C1/ru not_active IP Right Cessation
- 1990-11-05 NO NO90904796A patent/NO904796L/no unknown
- 1990-11-05 PT PT95781A patent/PT95781B/pt not_active IP Right Cessation
- 1990-11-05 HU HU907031A patent/HU208525B/hu not_active IP Right Cessation
- 1990-11-05 FI FI905467A patent/FI98814C/fi active IP Right Grant
- 1990-11-05 KR KR1019900017821A patent/KR0163956B1/ko not_active Expired - Fee Related
- 1990-11-06 PL PL28764290A patent/PL287642A1/xx unknown
- 1990-11-06 CN CN90108901A patent/CN1028169C/zh not_active Expired - Fee Related
- 1990-11-06 JP JP2302311A patent/JPH03169856A/ja active Pending
1995
- 1995-07-06 HK HK109895A patent/HK109895A/en not_active IP Right Cessation
1996
- 1996-03-08 CY CY185296A patent/CY1852A/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN107652215A (zh) *	2017-09-19	2018-02-02	重庆西南制药二厂有限责任公司	一种卡托普利的制备方法

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Publication number	Publication date
ATE119148T1 (de)	1995-03-15
FI98814C (fi)	1997-08-25
DE69017355D1 (de)	1995-04-06
NO904796D0 (no)	1990-11-05
ES2068349T3 (es)	1995-04-16
IE67284B1 (en)	1996-03-20
FI98814B (fi)	1997-05-15
HUT55754A (en)	1991-06-28
IL96018A (en)	1996-05-14
IL96018A0 (en)	1991-07-18
HK109895A (en)	1995-07-14
RU2001909C1 (ru)	1993-10-30
CA2027377A1 (en)	1991-05-07
IE903759A1 (en)	1991-05-08
CS540590A3 (en)	1992-11-18
EG18964A (en)	1994-09-29
CN1051908A (zh)	1991-06-05
AU6397790A (en)	1991-05-09
PL287642A1 (en)	1991-05-20
HU208525B (en)	1993-11-29
SK278604B6 (en)	1997-11-05
AU635341B2 (en)	1993-03-18
PH26962A (en)	1992-12-28
MX166721B (es)	1993-01-29
NZ235958A (en)	1993-01-27
PT95781A (pt)	1991-09-13
MY106445A (en)	1995-05-30
EP0427435A1 (en)	1991-05-15
ZA908523B (en)	1991-08-28
JPH03169856A (ja)	1991-07-23
EP0427435B1 (en)	1995-03-01
NO904796L (no)	1991-05-07
DK0427435T3 (da)	1995-03-27
HU907031D0 (en)	1991-05-28
CY1852A (en)	1996-03-08
FI905467A0 (fi)	1990-11-05
CZ277714B6 (en)	1993-03-17
KR910009657A (ko)	1991-06-28
KR0163956B1 (ko)	1998-12-01
US5026873A (en)	1991-06-25
DE69017355T2 (de)	1995-06-29
PT95781B (pt)	1997-11-28

Publication	Publication Date	Title
CN1028169C (zh)	1995-04-12	直接分离巯甲丙脯酸的方法
CN1883790A (zh)	2006-12-27	一种回收合成乙酰磺胺酸钾过程中所用催化剂的工艺
JPH0733244B2 (ja)	1995-04-12	リン酸二水素カリウムの製造方法
JPH08333312A (ja)	1996-12-17	バリンの精製法
US4052451A (en)	1977-10-04	Preparation of calcium pantothenate
US4076745A (en)	1978-02-28	Process for calcium salts α-ketocarboxylic acids
JP2828349B2 (ja)	1998-11-25	トリフルオロメタンスルホン酸スズの製造法
JPH034532B2 (pt)	1991-01-23
JPH08291135A (ja)	1996-11-05	タウリン類縁体の製造方法
JPS63250352A (ja)	1988-10-18	（ｒ）‐４‐アミノ‐３‐ヒドロキシブタン酸の製法
SU1549915A1 (ru)	1990-03-15	Способ очистки экстракционной фосфорной кислоты от фтора
JPH0737440B2 (ja)	1995-04-26	スルホニウム化合物の製造方法
US5097074A (en)	1992-03-17	Process for purifying 4,4'-dihydroxydiphenylsulfone
US4418016A (en)	1983-11-29	Method for recovering omega-amino-dodecanoic acid from crystallization mother liquors
DE69403109T2 (de)	1998-01-08	Verfahren zur Wiedergewinnung von L-Phenylalanin
JP3167516B2 (ja)	2001-05-21	タウリン精製に使用したアルコールの回収方法
JPH08134088A (ja)	1996-05-28	Ｎ−ホスホノメチルグリシンの単離方法
JPH01190661A (ja)	1989-07-31	４，４′−ジヒドロキシジフエニルスルホンの精製法
SU1018908A1 (ru)	1983-05-23	Способ получени иодата титана
JPH08157444A (ja)	1996-06-18	アミノエタンスルホン酸の製造方法
JPH07267922A (ja)	1995-10-17	カルボキシメチルシステインの製法
JPS6155914B2 (pt)	1986-11-29
JPH06306029A (ja)	1994-11-01	新規フェニルアラニン塩結晶とその製造法
DE19857690A1 (de)	2000-06-15	Verfahren zur Isolierung oder Reinigung von 2-Methyl-thiazolidin-2,4-dicarbonsäure
JPH0137984B2 (pt)	1989-08-10

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Date	Code	Title	Description
1991-06-05	C06	Publication
1991-06-05	PB01	Publication
1993-03-03	C10	Entry into substantive examination
1993-03-03	SE01	Entry into force of request for substantive examination
1995-04-12	C14	Grant of patent or utility model
1995-04-12	GR01	Patent grant
2002-04-24	C15	Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993)
2002-04-24	OR01	Other related matters
2011-02-02	C17	Cessation of patent right
2011-02-02	CF01	Termination of patent right due to non-payment of annual fee	Granted publication date: 19950412 Termination date: 20091207

CN1028169C - 直接分离巯甲丙脯酸的方法 - Google Patents

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